25. Dr. Robert Caldwell, St. Elsewhere (1983-1986)
Played By: Mark Harmon
Hottest Conquests: Joan Halloran (Nancy Stafford)
Promiscuity does not agree with Dr. Robert Caldwell (Mark Harmon), a plastic surgeon who arrive at St. Eligius Hospital in the second season of St. Elsewhere as the steady beau of hospital administrator Joan Halloran (Nancy Stafford). But when he is ready to take the next step and Joan is not, Bobby calls the whole thing off and embarks on a sexual bender.
Of course, it being the '80s and St. Elsewhere being mostly a drama, things do not end well for the good doctor; he was the first lead character in a show to contract the HIV virus and one of the first heterosexual ones. Two years after Caldwell's departure in season four (when he went to work in an AIDS hospice), the show made mention of his passing.